Francis Albert Sinatra: musician, actor, lover, legend and my idol since I first saw him singing on screen when I was eight. Incredibly, this December marks 100 years since he was born and The Voice became the soundtrack to so many lives.

Whether on stage or off, Sinatra’s mantra was, ‘all or nothing at all’ – either give it 100% or don’t even bother. It’s a mantra I believe true not just for life but for pitching too.  For as he said, “You can be the most artistically perfect performer in the world, but an audience is like a broad – if you’re indifferent, Endsville.”

So, as a rallying cry for the end of indifference and half-hearted pitching and in tribute to the Chairman of the Board, here’s my, “what would Frank do?” take on Caffeine’s Golden Rules of Pitching.

“Luck is fine, and you have to have luck to get the opportunity.  But after that, you‘ve got to have talent and know how to use it.” Use your talent. The brief has landed: get going.  Get a team meeting within the first 24 hours, appoint the pitch leader and agree roles.  Agree your battle-plan: client meetings, rehearsals; logistics etc. Unlike Sinatra, this bit isn’t sexy but it is necessary.

“Don’t tell me.  Suggest.  But don’t tell me.” Sinatra was a Driver and Drivers hate being told what to do. Not every client prospect will be like that; your job is to find out who you’re dealing with and what they really want.  Ask questions. Be in receive mode: shut up, listen and aim to bewitch but not bother or bewilder.

“My greatest ambition in life is to pass on to others what I know.” Be clear – and realistic – about what the prospect wants and why you are best placed to deliver it. Make recommendations – not a menu of options – and be clear on what you want the client to buy.

“You may be a puzzle, but I like the way the parts fit.” You’re pitching as a team and the client is buying a team.  Is your Rat Pack expert, entertaining, charismatic?  If you win, you and the client team will be spending a lot of time together.  Will you be the headline act they can’t wait to see or the forgettable warm up?

“Throughout my career, if I have done anything, I have paid attention to every note and every word I sing. If I cannot project this to a listener, I fail.”If a performer of Sinatra’s calibre has to rehearse, so do you.  Three timed rehearsals + one to an “outsider” 48 hours before the pitch. Identify key client questions and your answers and practice your opening and closing addresses.  What song are you going to leave your audience singing? (Metaphorically speaking).

“You’ve got to be on the ball from the minute you step out into that spotlight. You gotta know exactly what you’re doing every second on that stage, otherwise the act goes right into the bathroom. It’s all over. Good night.” If you’ve done your preparation thoroughly with the attention and obsession that Sinatra would be proud of, you’re ready to take centre stage.  Give the client a dynamic experience and avoid becoming a “prisoner” of the presentation. Engage the audience and connect with them emotionally, not just rationally by asking them interesting, relevant questions and demonstrating energy and enthusiasm when advocating your recommendations.  

“The big lesson in life, baby, is never be scared of anyone or anything.” Don’t be arrogant but do value what you have to offer.  You know you can help the client and you want to.  So don’t give up once the pitch ends.  Don’t disappear: address issues raised at the pitch and never stop until you have the result.

“The best is yet to come.” Whether you win or lose, demand feedback.  Act on what you’ve learnt and celebrate your wins with the client.

And, if there’s ever a stage in the process when you feel like giving up, keep going.

As Sinatra said, “The best revenge is massive success.”

The Caffeine Pitch Academy transforms business development in professional services including real estate, finance, marketing and law by teaching what it takes to win business: the principles and practices of successful pitching & salesmanship.  Contact [email protected] to learn more.


Louisa Clarke

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